


Jester's Guide to Life Drawings

by oftennot



Category: Critical Role (Web Series)
Genre: Discord: Widojest Love, Drawing, F/M, Flirting, Fluff, Oblivious? Jester, Paint me like one of your Zemnian girls, Pining Caleb, Widojest Secret Santa 2020
Language: English
Status: Completed
Published: 2020-12-20
Updated: 2020-12-20
Packaged: 2021-03-11 00:02:35
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,368
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28185822
Author URL: https://archiveofourown.org/users/oftennot/pseuds/oftennot
Summary: "Why don't you draw me?"The breath leaves his chest like Beauregard has sucker punched him. He hears the pounding of his heart in his ears, a warning to retreat."Y-you?" He stutters."Yeah! Isn't that a great idea?" Her smile is disarming, but it's not like Jester needed yet another tool in her arsenal to render him helpless.
Relationships: Jester Lavorre/Caleb Widogast
Comments: 8
Kudos: 96





	Jester's Guide to Life Drawings

**Author's Note:**

  * For [Bucket_of_kittens](https://archiveofourown.org/users/Bucket_of_kittens/gifts).



> Happy secret santa! 
> 
> The prompt was "Paint me like one of your Zemnian girls"

It's been 30 minutes precisely since Jester skipped over and sat herself next to Caleb on the ship's deck. He thought that this would be another instance of her trying to read over his shoulder as he transcribes his new spells, but she merely smiled at him and retrieved her own notebook and pencil from her bag and began drawing in earnest. Two minutes into their pleasant study session Jester started humming to herself, the melody occasionally interrupted by giggling.

Jester's presence is always a welcome one where Caleb is concerned. Her exuberance and idle chatter are pleasant and entertaining rather than irritating as others might expect. The fact that she hasn't thrown questions his way or attempted to steal his attention from his books is what distracts him. He glances at her from the corner of his eye, noting that her humming has quieted down and she's begun to sigh, tail whipping back and forth.

She is getting bored. He doesn't want her to leave just yet.

"What are you drawing?"

"I'm drawing a hot cup of cocoa."

"Are there dicks in it?"

"No, there's two very lovely marshmallows—"

"Mhm." Caleb glances up from his spell book, intrigued. He thought for sure there would be dicks.

Jester continues with the drawing. "That are just cozying up, schnuggling up next to each other."

"Yeah?" Caleb says, raising an eyebrow.

"With consent," she adds.

"We're not talking about grass, are we?" He asks after a moment.

Jester finally looks up from her sketchbook. "No, I'm talking about marshmallows," she says like it's obvious. Which, he supposes, it is.

"Marshmallows."

"Yeah."

"Felt like there was a hidden meaning there, for a moment."

She shakes her head innocently. "No."

"Okay."

They share a smile.

"Just marshmallows. Marshmallows with wings, marshmallows with staffs. Marshmallows." She shrugs.

"Okay," Caleb nods. There is something more to it, but if Jester is not electing to share then he will not push her. "I see."

He's returning his attention to his books when she speaks up, "Do you wanna try?"

"Try what?"

"Drawing!" She holds her sketchbook and pencil out to him. Caleb rears back in surprise, clutching his own parchment and quill to his chest.

"Oh, uh, no. That is alright," he declines, shooting Jester an apologetic smile in response to her encouraging one. "I wouldn't want to clutter your works of talent with my scribbles."

Jester tuts at him. "I bet you're really good at drawing, Caleb. You're super creative and make _amazing_ things with your spells all the time! Like at Travelercon!"

Caleb attempts to hide his blushing cheeks in the folds of his new scarf. Memories of all the illusions and images he cast on the island of Rumblecusp are called to mind. Glittering archways, iridescent dicks, fiery red hair and tricksy smiles, tiny blue pixies fluttering about, and Jester's grinning face in the night sky, winking down at the island's inhabitants like the stars surrounding her.

"That was different," he says, because it is in his mind. Caleb didn't consider his magic _art_ , per se. He was trying to create something beautiful, but only because it was for Jester. Normally his spells are about protecting his family or smiting their enemies. Magic is a utility with a specific purpose. Those illusion spells were also serving a purpose—to help Jester with something of vital importance. If his creations were art, it's because he was envisioning what Jester would want and what would make her happy. _She_ is the artist.

"How is it different?" Jester questions him. She's still holding her materials out to Caleb, waiting for him to take it.

His mouth opens and closes repeatedly as he formulates a reply that will not reveal the depths of his affection for her. "What I did was—it was nothing, really. Just a bit of magic. It certainly can't hold a candle to the art you make." He nods at the sketchbook.

Her jaw falls open. " _Nothing?_ It was _not_ nothing, Caleb. It was—" the bells dangling off her horns jingle as she shakes her head, interrupting her train of thought. The hand grasping her pencil comes up in a halting gesture. "Okay, no. I can't even believe we're having this conversation. Why don't you just try, Caleb? It doesn't have to be good, it's about having fun!"

He is still wary and it reflects in the downturn of his lips. Jester pouts at him, fluttering her lashes. "Please, Caleb?"

His heart seizes. He knows the battle is lost. There was never a chance. He was a goner the second she sat down next to him and started humming as she doodled on the paper. His eyes close and he lets out a sigh of resignation.

" _Ja,_ sure. Okay."

"Yes!" Jester wiggles in excitement. "I promise this is going to be so much fun."

"I'll take your word for it."

He takes the pencil and sketchbook from her. The pencil is warm from being held in her hand for a half hour and the grip is smooth. The pages of the sketchbook are a crisp white, the edges creased from frequent turning. The current page displays a drawing of a cup of cocoa with two marshmallows floating closely together. Schnuggling, perhaps. What appears to be wings protrude from behind one and a quarterstaff rests up against the other.

"Should I use a different page?" he asks, gesturing down to her recent sketch.

"Sure," Jester nods and leans forward, flipping to a new page for him. The smell of lavender wafts from her hair. "You should have a fresh, blank canvas to create upon."

Caleb chuckles. "You make it sound so serious."

"Drawing is serious business."

"I thought it was supposed to be fun?"

"It can be both."

"Right," he says, unable to hold back a smile. He clears his throat. "Time to get to work then." Jester nods her head eagerly. He can feel her expectant eyes on him like the heat of the sun in this cloudy, frigid climate. His finger starts tapping on the book. The blank page stares back at him, its emptiness loud and mocking. He lifts the pencil up to the paper but stops mere centimeters away from making contact, and his hand falls back to his side. This process repeats itself a number of times before Jester speaks up.

"What's the matter, Caleb?"

"I'm not sure what I should draw," he confesses.

"Hmm," Jester's lips purse and she tilts her head in thought. "What do you usually think about when you make those really cool spells? Like, what's your inspiration?" She prompts, adding the bit at the end when she sees his brows furrowing and mistakes the expression for confusion. In truth she, Jester, is his muse. There is no way he will admit that.

"Usually I take into consideration the spell's purpose," he says instead because it is partly the truth, "and cast it accordingly."

Her face twists endearingly as she processes this, clearly finding his answer odd, but it smooths out into another smile. Her eyes light up with an idea. Caleb prepares himself to be thrown for a loop yet again by Jester Lavorre.

"I got it! Why don't you draw me?"

The breath leaves his chest like Beauregard has sucker punched him. He hears the pounding of his heart in his ears, a warning to retreat.

"Y-you?" He stutters.

"Yeah! Isn't that a great idea?" Her smile is disarming, but it's not like Jester needed yet another tool in her arsenal to render him helpless.

"Aren't figure studies more difficult?" Caleb tries to save himself, struggling against the tide threatening to drag him under. "Wouldn't it be better to start small? Like with an... apple, or something."

Jester scoffs and waves away the suggestion like it's ludicrous. "Drawing fruit is _boring._ Trust me. People are much more interesting to draw!"

She nudges him with her elbow. "And I'm _pretty_ interesting, don't you think?"

"Yes, of course," Caleb answers automatically, because he cannot lie to her. Not anymore. He can, however, not make an utter fool of himself. "Perhaps I can work my way up to drawing you, after I've practiced with other references. Under your tutelage."

"Well, if I'm teaching you, then my first lesson is to just jump right into the deep end." She grins, believing her words to have settled the matter. (They had.)

"So it's sink or swim then, Miss Lavorre?"

"Aw, you make it sound so scary, Caleb. I'm just making a suggestion based on what you said."

He gives her an amused smile. "I don't remember saying anything about taking a swim."

"Not that," her tail flicks at his wrist but there's no real force behind it. "I meant about your art's purpose." His immediate reaction is to correct her that he does not make art, but he refrains. Jester has made up her mind and who is he to change that?

"I asked you to draw, so technically this is for me." She says, catching his eye. Caleb wonders if she has seen right through him. The thought both petrifies and excites him, and the result is fire burning through his veins. "And I want you to draw me. I'm always drawing other people but I never get a portrait of myself!"

"If it's a gift for you, Jester, then I will gladly do what I can." He nearly regrets his words the moment they leave his lips, fearing that he's said too much, but the way appreciation shines through her expression dispels such negative thoughts from his mind.

Of course he will do this for her. He would do anything for Jester.

One finger pulls at the scarf wrapped snug around his neck, suddenly feeling warm despite the frigid temperatures of the waters they're sailing. His palms have become clammy and his grip on the pencil now falters. His eyes dart around the deck, checking if anyone is watching them. The crew is occupied with sailing and the associated duties. Fjord is speaking with the captain of the vessel, Beauregard standing by his side, nodding along as if she understands any of the nautical terms no doubt being used. The three remaining members of the Mighty Nein are not currently on deck, and that suits Caleb just fine. The fewer prying eyes to witness his embarrassment the better.

Jester adjusts her positioning, brushing errant strands of hair out of her face and straightening her coat. Caleb discreetly wipes his hand on his trousers before once again bringing the pencil up to the awaiting page. There is no turning back now.

He assesses Jester. She's beaming at him, bright enough to illuminate the way for their ship on this dark and dreary day. Caleb's cheeks heat up and he ducks his head down, focusing on the paper. _Scheisse,_ he can do this. Treat it like any other mission, like an assignment. Start with the basics. During his brief years of schooling he had some instruction in art and drawing. The pencil begins to sketch a circle, then adding a cross down the center to adjust for proportions. He considers whether or not to include the rest of the body, but decides he'd better not. There is only so much one wizard can handle in a day.

The groundwork finished, Caleb looks back at Jester. Her gaze is still trained on him, smile held in place though it's beginning to twitch under strain. Her tail flicks in the air, an unconscious habit of hers when she gets restless. Her eyes dart back and forth between his face and the sketchbook. He chuckles at her obvious impatience and reluctance to sit still.

Leave it to Jester to make him feel at ease even while she is the source of his current stress. "You don't need to strain yourself like this. If you want to move and talk, that's alright. A little conversation will help me relax as well."

 _"Thank you,"_ Jester sighs in relief. "That was torture."

"Do you enjoy drawing people the most?" Caleb asks, hoping to spur the tiefling into one of her detailed explanations. He finds it's easier to study her when he is not the object of her attention.

Her lips part and words pour forth like a dam broken. Caleb allows himself to be swept up in her current. Her voice is warm and comforting. He nearly forgets that they're sitting on a ship in the middle of a cold, desolate ocean.

"People are really fun to draw! They make so many different faces, some super funny expressions. Like, how Beau looks like she's holding her breath when Yasha walks by—not because Yasha's stinky or anything—but like Beau is trying to be cool and tough or something. And the dreamy look Yasha gets on her face when she's staring at Beau and her abs."

Jester sighs as she imagines their two friends, both usually strong and put together, fall into blubbering messes around each other. Her eyes twinkle, lips upturned in a sweet smile, her round cheeks flushed purple from the cold. _There,_ Caleb thinks. That's the woman he loves. In love with love. Happy from others happiness. His hand moves, copying the slant of her nose onto the page.

"What is the funniest face you've seen someone make?" He prompts her to continue. Even without the needed distraction he wouldn't mind listening to her ramble all day.

Her fangs bite into her lips as Jester chuckles deviously, a finger tapping at her chin. The tip of the pencil traces the delicate lines of her jaw and neck. "Hehe. That's a hard one. Hmm... maybe it was the look of outrage on Lord Sharpe's face when I dropped my disguise as mama and he realized it was _me_ that led him onto the balcony."

"I bet that was quite the sight to behold. I wish I could've been there to see it."

"Oh, it was pretty great. You would've loved it." Her gaze remains blessedly off of him, staring into the sky as her mind races through the memories.

"What initially piqued your interest in art?" He asks.

She's quiet as she contemplates her answer. Silences with Jester are just as loud as her conversations, but Caleb knows to give her the space and time to respond. The sun also takes reprieve behind clouds from time to time, but there is always the assurance that it will reappear.

"Mama got me a lot of tutors. Even if I couldn't go to a real school she thought it was important that I get a good education. I was really good at art. I had tons of books and reading to do, but that got boring after a while." Caleb smiles ruefully but Jester takes no notice. "I didn't want to read _other_ people's stories about adventures. I wanted one of my own! Drawing was a bit like that. I could create my own stories, almost like I was out there experiencing it myself."

Like she always does, Jester smiles through her pain. It's convincing, the mask she wears. Her mother taught her well. But careful observation reveals the cracks in her facade. The strain in the creases of her eyes, the subtle trembling of her lips, how high her voice pitches as she forces the sadness in and the false cheer out. Caleb was trained to observe, to notice, to understand that which people try to hide. These skills were learned with the intent to manipulate and gain power over others, but that was Bren. Hurting Jester goes against every fiber of Caleb's being. He can perhaps use this to help or comfort her in some small way. Pain he understands well, the haunting memory forever etched into his skin. He knows what it is to mourn time lost by no fault of your own; time that was taken from you. 

_It's okay,_ he wants to tell her. _You can be sad._

Instead, he tries to show her. In the slight shadow over her eyes, the furrow of her brows. This too is part of Jester and it deserves to be seen, even if she is the only one to see it. So she can understand how this does nothing but complete the picture of who she is.

The last few minutes he spends sketching pass in silence. Caleb is lost in his new found determination to finish his drawing, Jester in her thoughts. She seems to have forgotten that she is being drawn. She startles when Caleb sits back, setting the pencil down onto the page with a satisfied sigh. She leans over to sneak a peek at the finished product.

He places a hand over it. "Aw, Caleb, I wanna see it!"

"Before you do," he says, eyes only making it up as far as her stockings. "You must promise me that you won't laugh."

"I _promise._ "

"Pinky swear?" He holds his finger up to her.

She wraps hers around it tightly. "Pinky swear."

"Alright." With great trepidation he returns Jester's sketchbook to her, face turned in the opposite direction so he doesn't have to witness her reaction.

A beat of silence. Caleb swallows. 15 seconds, 16, 17, 18—she hasn't said anything, she must hate it.

The sound of sniffling. His head whirls around, heart leaping to his throat. _Scheisse,_ this is worse than he thought. She didn't just hate it, he made her _cry._

"Jester, I'm sorry, please—"

"It's beautiful," she interrupts.

"Er, what?"

"It's beautiful, Caleb."

Her face is flushed a darker purple, freckles standing out like the first drops of freshly fallen snow. Unshed tears have built up in the corners of her eyes. One blink breaks the tension holding them and a few drops roll down her cheeks. Caleb watches their path, curving around her smile. Now she's looking right at him and suddenly he finds it hard to breathe.

His lips move automatically, saying what his mind cannot, "You... you like it?"

"I love it." Her voice breaks around the word 'love' and Caleb's blood burns like fire.

"It-it's really not much. There are better artists out there than I."

A gloved hand comes to rest on top of his. He blinks at Jester. "No other artist could've made this. It's your work, Caleb, and it's wonderful. Really. Thank you." She squeezes his hand to emphasize her gratitude. He should probably say something in reply, but he is captive to her eyes and smile and hand around his. She saves him from having to give a response by rising abruptly, skirts twirling, and gathering her sketchbook and pencil.

"First thing's first!" She says, and Caleb's mind finally catches up to the present.

"Erm, what would that be?"

She grins down at him, her eyes still a bit glassy and face a lovely violet. "I have to find a way to frame this."

His instinct is to offer more protests, to insist that it's just scribbles—but then he notices that her gaze is back on the page, how the air itself lights up in response to her palpable joy. The warm, wistful smile that graces her lips, how her eyes soften and she lets out a sigh that is nearly lost to the wind. Caleb's mouth clamps shut and he swallows down whatever words he was about to foolishly say. His heart is rattling inside his chest, but this time it does not hurt. This time it feels... hopeful.

"I may be of some assistance with that," he offers. "I can transmute some wood or metal into a frame, if you'd like."

"Oh, Caleb," her lips part as if she's about to say something more, but then she reaches down and grabs his hand, hauling him to stand. "Let's go."

He feels a tentative smile work its way onto his face. Things always felt easier and more natural in Jester's presence. He's surprised by how steady his hand is in hers. Jester giggles, and then he's pulled along as she races across the deck and down the stairs to the levels below.

"This is going to be _so_ much fun!" She cheers.

Caleb agrees.


End file.
